Sometimes the best upgrade you can make is to your content - invest in your music; explore new streaming services or simply buy some more vinyl/downloads/CDs.
Sit back, enjoy the music, and then only think about your next hardware move when the funds and brain-space allow.
We’re here for the long game: the more you enjoy the music, the more you’ll enjoy Naim 
I liked the brief but very accurate observation from the late Derek Jenkins. A small group of us were watching him assemble an LP12 in its support jig. His comment seemed to hit the spot.
“There’s always more”.
True. Once you “let go” of the hardware mania and listen to music as it’s meant to then the equipment start to shine. It’s when updating hardware you go into AB mode and it can be really stressful and in many cases the main reason why you many times think more expensive equipment is inferior to what you have because you don’t listen with the same ears anymore.
Can you do something to make 80’s pop music sound good?
In many cases, that would require a time machine to go back and prevent serious crimes against recording quality!
But seriously…there are some decent remasters of classic 1980s stuff.
Didn’t Naim develop the flux capacitor for the Statement?
It’s all about retaining the balance. I was in a similar situation to yourself a few months back with 252DR/250DR/NDX2:555PSDR. I knew my ideal end game was ND555/552DR and was in a quandary about which to upgrade first (ND555).
The point is, I wouldn’t have jumped to the ND555 without at least knowing I could also move to the 552 if desired. The two work beautifully together.
G
The reason why I feel afraid to upgrade is the guilt I feel from spending the money when I could have spent it on someone more deserving.
Hair shirts are overrated.
Enjoy what you have worked for.
Plumtree’s Potted Meat.
Without it, my life is incomplete.
[Sorry, but you gotta swop that Cisco for an EE8.]
On this basis I probably shouldn’t have started at all, I look at my kit, much of it secondhand and I feel sick.
Looking at your system details it’s similar to my system and looks very well balanced. Perhaps your speakers could be looked at but if they work really well in your room you could end up with worse performance spending more money.
From my personal experience of listening to components higher up the chain you have to spend a large sum of money to get a small incremental increase in performance. Some will find it worthwhile and have the funds to do so. Myself I’m happy with my system also and do not see the value in the large outlay to upgrade vs what I currently have. Others will no doubt disagree.
Enjoy your system and maybe get some new music instead.
Derek once said to me when I played Richard Thompson’s How Will I Ever Be Simple Again at a turntable demo “That would sound good on a Dansette”. It always stuck with me, it’s great to focus on the music rather than the system. It’s a great place to be when you’re not thinking about the next pice of kit, but just enjoying the music.
Well not quite afraid but if it sounds good, that’s because it is good. Buy some more music.
Don’t let your gear disappoint you in any way not everyone can afford high end gear. Unfortunately it seems to be the norm on here. All my gear is second hand but in superb condition it’s taken me 15 years to achieve my setup.
The only brand new item is the speakers the first time I’ve been able to afford new ones. They will be my last before I retire. You have to be honest with yourself and say enough is enough I’m happy with my setup.
I’m going to invest in more music and enjoy it rather than the system.
Let’s face it when you flat line it’s not going with you 
harsh statement I know but I had a friend who passed away. His other half with no hesitation put all gear on flee bay straight away it went very quickly for little money
I have said it before and arts worth saying again. There is no ’ bad’ Naim kit. It is all high end and only gets better with listening to the music.
It’s the nature of the game to want to try changes in the pursuit of making what you have better in whatever way. I tend to apply the rule of Time (to listen), Money (for kit changes) and space (better inevitably requires more of this). In my case, unless I find myself with a significant increase in time to enjoy any bettering of what I have, I force myself to use the time I do actually have to do more listening rather than looking at kit options and in doing so realise what I have is a whole lot better than what a lot of people could ever dream of calling their music system.
The fact that many folks on here have immeasurably enjoyable systems that are decades old is testament to the staying power of Naim as a brand, you could still spend a rather modest sum on a vintage Naim setup and it would still sound better than a lot of what can be bought new today.
Thank you for your thoughtful reply @omegaman, its not that I am disappointed with my system, I easily justified their secondhand cost at the time, but on reflection it wasn’t a sensible use of resources.
Different and more money doesn’t mean more enjoyment or involvement , I just reread the first edition of HiFi plus magazine whilst rearranging the garage (my word I wish that publication had stayed the same) and the review of my Densen Beat B100 amp absolutely nails it.
I still have that Densen system and it is going nowhere , it is stunning and has Guru Qm10 speakers on the end of it, it’s perfectly balanced and puts a smile on the face like nothing else.
My other system is Naim, and I adore it, but the Densen is unreal, only wish there were still killer components like those around today.
It seems there just aren’t any big steps forward in Hi-fi reproduction nowdays. Source’s have obviously had radical developments but we are still discusiing if they are better or worse.
Over the last 20 years system’s seem to have been tweaked forward without any big and significant improvement so have we reached “peak” Hi-fi?